Skysail Real Estate

There are 22 active listings in Skysail, Naples, with a median asking price of $560,851 and an average of 73 days on market.

Active Listings

Median Asking Price

$560,851

Average Asking Price

$587,393

Avg. Days on Market

Closed · Last 90 Days

About Skysail

Skysail is a Southwest Florida community in Naples where the NABOR MLS currently shows 22 active listings, asking $345,525 to $1,180,661, averaging 73 days on market, with 5 closed sales recorded here in the last 90 days. Waterfront Realty Group, Inc. has worked this market as an independent, Realtor-owned brokerage since 1986, and pairs every customer with a Sales Associate who knows these streets, waterways, and price trends firsthand.

Figures reflect the active Skysail inventory shown on this page, drawn live from the Naples Area Board of REALTORS® (NABOR) MLS. Closed-sale counts cover the trailing 90 days.

Available Properties

Skysail Listings

22 properties shown

$1,180,661

4310 Cepheus WAY

3 bd · 3 ba · 2,698 sf

Listing courtesy of Neal Communities Realty, Inc.

Source: NABOR MLS

$895,900

3995 Pegasus WAY

5 bd · 5 ba · 3,393 sf

Listing courtesy of ND Realty

Source: NABOR MLS

$758,102

4647 SkySail DR

3 bd · 2.5 ba · 2,427 sf

Listing courtesy of Neal Communities Realty, Inc.

Source: NABOR MLS

$700,000

4065 Aquila PL

3 bd · 3 ba · 2,456 sf

Listing courtesy of John R Wood Properties

Source: NABOR MLS

$697,900

4056 PEGASUS WAY

3 bd · 2.5 ba · 2,233 sf

Listing courtesy of Realty One Group MVP

Source: NABOR MLS

$669,404

4239 Pegasus WAY

4 bd · 3 ba · 2,332 sf

Listing courtesy of Neal Communities Realty, Inc.

Source: NABOR MLS

$657,185

4691 SkySail DR

3 bd · 2 ba · 2,309 sf

Listing courtesy of Neal Communities Realty, Inc.

Source: NABOR MLS

$649,000

4003 Pegasus WAY

3 bd · 2.5 ba · 1,966 sf

Listing courtesy of Coldwell Banker Realty

Source: NABOR MLS

$624,900

4101 Pegasus WAY

3 bd · 2.5 ba · 2,064 sf

Listing courtesy of Compass Florida, LLC

Source: NABOR MLS

$585,000

4154 Pegasus WAY

4 bd · 3 ba · 2,351 sf

Listing courtesy of Realty One Group MVP

Source: NABOR MLS

$566,802

4671 SkySail DR

2 bd · 2 ba · 1,904 sf

Listing courtesy of Neal Communities Realty, Inc.

Source: NABOR MLS

$554,900

4564 Centaurus CIR

3 bd · 2 ba · 1,859 sf

Listing courtesy of Realty One Group MVP

Source: NABOR MLS

$554,621

4236 Pegasus WAY

3 bd · 2.5 ba · 2,064 sf

Listing courtesy of Neal Communities Realty, Inc.

Source: NABOR MLS

$509,000

3980 Pegasus WAY

3 bd · 2 ba · 1,812 sf

Listing courtesy of John R Wood Properties

Source: NABOR MLS

$496,500

4475 Centaurus CIR

3 bd · 2 ba · 1,860 sf

Listing courtesy of Neal Communities Realty, Inc.

Source: NABOR MLS

$495,736

4467 Centaurus CIR

3 bd · 2 ba · 1,778 sf

Listing courtesy of Neal Communities Realty, Inc.

Source: NABOR MLS

$454,900

4636 Skysail DR

3 bd · 2 ba · 1,848 sf

Listing courtesy of Realty One Group MVP

Source: NABOR MLS

$439,900

4653 Centaurus CIR

3 bd · 2 ba · 1,548 sf

Listing courtesy of Realty One Group MVP

Source: NABOR MLS

$384,420

5093 Draco CIR

3 bd · 2.5 ba · 1,994 sf

Listing courtesy of Neal Communities Realty, Inc.

Source: NABOR MLS

$355,517

5042 Draco CIR 2906

3 bd · 2.5 ba · 1,507 sf

Listing courtesy of Neal Communities Realty, Inc.

Source: NABOR MLS

$346,780

5129 Draco CIR 0105

3 bd · 2.5 ba · 1,790 sf

Listing courtesy of Neal Communities Realty, Inc.

Source: NABOR MLS

$345,525

5034 Draco CIR

3 bd · 2.5 ba · 1,507 sf

Listing courtesy of Neal Communities Realty, Inc.

Source: NABOR MLS

Listing data provided via the Naples Area Board of REALTORS® (NABOR) MLS. Information deemed reliable but not guaranteed. Equal Housing Opportunity. © 2026 Waterfront Realty Group, Inc. License CQ257718. All rights reserved.

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